KR20110026197A - Organic photoresist stripper composition - Google Patents
Organic photoresist stripper composition Download PDFInfo
- Publication number
- KR20110026197A KR20110026197A KR1020090083992A KR20090083992A KR20110026197A KR 20110026197 A KR20110026197 A KR 20110026197A KR 1020090083992 A KR1020090083992 A KR 1020090083992A KR 20090083992 A KR20090083992 A KR 20090083992A KR 20110026197 A KR20110026197 A KR 20110026197A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- group
- compounds
- aminobutan
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 71
- -1 hydroxyl cycloalkane compounds Chemical class 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 38
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 9
- 150000005846 sugar alcohols Chemical class 0.000 claims abstract description 9
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 8
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 35
- 229930195733 hydrocarbon Natural products 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical group [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- 235000010356 sorbitol Nutrition 0.000 claims description 5
- 150000008163 sugars Chemical class 0.000 claims description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 claims description 4
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 4
- 229960000367 inositol Drugs 0.000 claims description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 4
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- JRLAKNMVEGRRGK-UHFFFAOYSA-N 1-(ethylamino)butan-2-ol Chemical compound CCNCC(O)CC JRLAKNMVEGRRGK-UHFFFAOYSA-N 0.000 claims description 2
- RDTCWQXQLWFJGY-UHFFFAOYSA-N 1-(methylamino)butan-2-ol Chemical compound CCC(O)CNC RDTCWQXQLWFJGY-UHFFFAOYSA-N 0.000 claims description 2
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 claims description 2
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 claims description 2
- MPGVRLGIUWFEPA-UHFFFAOYSA-N 1-aminooctan-2-ol Chemical compound CCCCCCC(O)CN MPGVRLGIUWFEPA-UHFFFAOYSA-N 0.000 claims description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
- FVRSWMRVYMPTBU-UHFFFAOYSA-M 1-hydroxypropyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCC(O)[N+](C)(C)C FVRSWMRVYMPTBU-UHFFFAOYSA-M 0.000 claims description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 2
- QHBWSLQUJMHGDB-UHFFFAOYSA-N 2,3-diaminopropan-1-ol Chemical compound NCC(N)CO QHBWSLQUJMHGDB-UHFFFAOYSA-N 0.000 claims description 2
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims description 2
- BMTAVLCPOPFWKR-UHFFFAOYSA-N 2-(ethylamino)butan-1-ol Chemical compound CCNC(CC)CO BMTAVLCPOPFWKR-UHFFFAOYSA-N 0.000 claims description 2
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 claims description 2
- SGBGCXQCQVUHNE-UHFFFAOYSA-N 2-(ethylamino)propan-1-ol Chemical compound CCNC(C)CO SGBGCXQCQVUHNE-UHFFFAOYSA-N 0.000 claims description 2
- HSHIHFMFJLIQDN-UHFFFAOYSA-N 2-(methylamino)butan-1-ol Chemical compound CCC(CO)NC HSHIHFMFJLIQDN-UHFFFAOYSA-N 0.000 claims description 2
- PXWASTUQOKUFKY-UHFFFAOYSA-N 2-(methylamino)propan-1-ol Chemical compound CNC(C)CO PXWASTUQOKUFKY-UHFFFAOYSA-N 0.000 claims description 2
- BCLSJHWBDUYDTR-UHFFFAOYSA-N 2-(propylamino)ethanol Chemical compound CCCNCCO BCLSJHWBDUYDTR-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 2
- VPSSPAXIFBTOHY-UHFFFAOYSA-N 2-amino-4-methylpentan-1-ol Chemical compound CC(C)CC(N)CO VPSSPAXIFBTOHY-UHFFFAOYSA-N 0.000 claims description 2
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 claims description 2
- DPEOTCPCYHSVTC-UHFFFAOYSA-N 2-aminohexan-1-ol Chemical compound CCCCC(N)CO DPEOTCPCYHSVTC-UHFFFAOYSA-N 0.000 claims description 2
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 claims description 2
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 2
- ZFDNAYFXBJPPEB-UHFFFAOYSA-M 2-hydroxyethyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCO ZFDNAYFXBJPPEB-UHFFFAOYSA-M 0.000 claims description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 2
- AXCSUIBUZBQBGT-UHFFFAOYSA-N 3-(ethylamino)butan-1-ol Chemical compound CCNC(C)CCO AXCSUIBUZBQBGT-UHFFFAOYSA-N 0.000 claims description 2
- FBXBSCUQZWUZDD-UHFFFAOYSA-N 3-(ethylamino)propan-1-ol Chemical compound CCNCCCO FBXBSCUQZWUZDD-UHFFFAOYSA-N 0.000 claims description 2
- HNNZBZKURNBXOO-UHFFFAOYSA-N 3-(methylamino)butan-1-ol Chemical compound CNC(C)CCO HNNZBZKURNBXOO-UHFFFAOYSA-N 0.000 claims description 2
- KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 claims description 2
- AGMZSYQMSHMXLT-UHFFFAOYSA-N 3-aminobutan-1-ol Chemical compound CC(N)CCO AGMZSYQMSHMXLT-UHFFFAOYSA-N 0.000 claims description 2
- LXHUAPWNXDAINJ-UHFFFAOYSA-N 3-aminoheptan-4-ol Chemical compound CCCC(O)C(N)CC LXHUAPWNXDAINJ-UHFFFAOYSA-N 0.000 claims description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 2
- DBKSSENEKWOVKL-UHFFFAOYSA-N 4-(methylamino)butan-1-ol Chemical compound CNCCCCO DBKSSENEKWOVKL-UHFFFAOYSA-N 0.000 claims description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 claims description 2
- CTDFCRIOSLTKFQ-UHFFFAOYSA-N 5-aminooctan-4-ol Chemical compound CCCC(N)C(O)CCC CTDFCRIOSLTKFQ-UHFFFAOYSA-N 0.000 claims description 2
- VJGRDSFPHUTBBE-UHFFFAOYSA-N 5-aminopentan-2-ol Chemical compound CC(O)CCCN VJGRDSFPHUTBBE-UHFFFAOYSA-N 0.000 claims description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229940102253 isopropanolamine Drugs 0.000 claims description 2
- KTDMLSMSWDJKGA-UHFFFAOYSA-M methyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](C)(CCC)CCC KTDMLSMSWDJKGA-UHFFFAOYSA-M 0.000 claims description 2
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 claims description 2
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 2
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- PVNNOLUAMRODAC-UHFFFAOYSA-N 4-(ethylamino)butan-1-ol Chemical compound CCNCCCCO PVNNOLUAMRODAC-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 239000011368 organic material Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 16
- 238000005260 corrosion Methods 0.000 description 16
- 230000007797 corrosion Effects 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000004380 ashing Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000005468 ion implantation Methods 0.000 description 8
- 238000001020 plasma etching Methods 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical group OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 2
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- 229930182830 galactose Natural products 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 125000002951 idosyl group Chemical class C1([C@@H](O)[C@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005389 semiconductor device fabrication Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/261—Alcohols; Phenols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
- C11D2111/22—Electronic devices, e.g. PCBs or semiconductors
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Cleaning Or Drying Semiconductors (AREA)
Abstract
Description
본 발명은 유기계 포토레지스트 제거용 조성물에 관한 것으로서, 보다 상세하게는 평판표시장치 또는 반도체장치의 제조 공정에 있어서, 기판으로부터 포토레지스트, 포토레지스트 잔사물, 이온주입공정을 통해 경화된 포토레지스트 등을 박리하기 위한 유기계 포토레지스트 제거용 조성물에 관한 것이다. The present invention relates to a composition for removing an organic photoresist, and more particularly, to a photoresist, a photoresist residue, a photoresist cured through an ion implantation process, and the like from a substrate in a manufacturing process of a flat panel display or a semiconductor device. It relates to a composition for removing an organic photoresist for peeling.
평판표시장치 또는 반도체 장치의 제조는, 금속막 또는 절연막층을 형성하는 공정, 포토레지스트층을 형성하는 공정, 포토레지스트에 마스크 패턴을 전사하는 노광 공정, 패턴을 따라 막을 에칭하는 식각공정 및 포토레지스트를 제거하는 박리공정으로 진행된다. 최근 배선 간격이 좁아짐에 따라 반응성 가스를 이용한 드라이에칭 및 고온에싱 공정이 반도체 공정 중 중요한 공정으로 자리잡아가고 있다. 이들 공정에 의해 폴리머가 절연막 또는 금속막에 강하게 응착되어 형성되는 잔사물이 발생된다. 이러한 포토레지스트 잔사, 즉 폴리머는 포토레지스트 박리액으로 제거하는 것이 보통이다. The manufacture of a flat panel display or a semiconductor device includes a process of forming a metal film or an insulating film layer, a process of forming a photoresist layer, an exposure process of transferring a mask pattern to the photoresist, an etching process of etching a film along the pattern, and a photoresist. It proceeds to the peeling process of removing. Recently, as the wiring spacing becomes narrower, dry etching and high temperature ashing processes using reactive gases are becoming important processes in the semiconductor process. These processes produce residues formed by strongly adhering a polymer to an insulating film or a metal film. Such photoresist residues, i.e., polymers, are usually removed with a photoresist stripper.
또한 반도체 공정 중 생산라인 전단에서 소오스/드레인을 형성하는 이온주 입 공정은 3족 또는 5족의 이온을 실리콘의 표면을 뚫고 들어갈 만큼 큰 에너지를 갖도록 전기장으로 가속하여 실리콘 속으로 주입하는 공정으로 실리콘에 불순 이온을 도핑하여 부분적으로 전도도, 문턱전압 등의 전기적 성질을 바꾸기 위한 목적으로 수행되는 공정이다. 소오스/드레인 영역을 형성하기 위해서는 높은 도즈(dose)량의 이온주입공정을 거치므로 포토레지스트 상부의 경화가 가속화된다. 따라서 이 포토레지스트를 제거하는 것은 매우 어렵다. 이러한 포토레지스트를 제거하기 위해 고온에싱처리를 할 경우 포토레지스트의 부피는 줄지만 포토레지스트막의 경화가 심화되고 또한 포토레지스트 내부의 압력 상승으로 인한 퍼핑 작용에 의해 폴리머가 형성되므로 이들 역시 제거하기가 어렵다. In addition, the ion implantation process that forms the source / drain at the front of the production line during the semiconductor process is a process in which the ions of group 3 or 5 are accelerated into an electric field and injected into the silicon so that the energy is large enough to penetrate the surface of the silicon. It is a process performed for the purpose of partially changing the electrical properties such as conductivity, threshold voltage by doping impurity ions. In order to form the source / drain regions, a high dose amount of ion implantation is performed to accelerate curing of the upper portion of the photoresist. Therefore, it is very difficult to remove this photoresist. When the high temperature ashing treatment is performed to remove the photoresist, the volume of the photoresist decreases, but since the curing of the photoresist film is intensified and the polymer is formed by the puffing action due to the pressure increase inside the photoresist, it is difficult to remove them. it's difficult.
이러한 포토레지스트, 플라즈마 에칭 또는 고온 에싱 공정 후 잔류하는 포토레지스트 잔사물, 이온주입 후 경화된 포토레지스트 및 퍼핑 작용에 의해 형성된 폴리머를 제거하는 포토레지스트 제거용 조성물로는, 아민계 조성물, 히드록실아민 화합물로 구성되는 조성물 등이 공지되어 있다. 예를 들면 미국 특허공보 제 4,617,251호는 특정 아민 화합물[예컨대, 2-(2-아미노에톡시)에탄올, 2-(2-아미노에틸아미노)에탄올, 또는 이들의 혼합물] 및 극성용매(예컨대, N-메틸-2-피롤리돈(NMP), 테트라히드로푸르푸릴알코올, 디메틸글루타레이트, 술포란, 감마-부틸락톤(GBL), N,N-디메틸아세트아미드 및 이들의 혼합물)를 함유하는 포지형 포토레지스트 제거용 조성물에 대해 개시하고 있고, 미국 특허공보 제5,279,771호는 히드록실아민, 알칸올아민 및 임의의 극성용매를 포함하는 포토레지스트 제거용 조성물을 개시하고 있다. As the photoresist removal composition for removing the photoresist, the photoresist residue remaining after the plasma etching or the high temperature ashing process, the photoresist cured after ion implantation, and the polymer formed by the puffing action, an amine composition and hydroxylamine Compositions composed of compounds and the like are known. For example, US Pat. No. 4,617,251 discloses certain amine compounds [eg, 2- (2-aminoethoxy) ethanol, 2- (2-aminoethylamino) ethanol, or mixtures thereof) and polar solvents (eg, N -Methyl-2-pyrrolidone (NMP), tetrahydrofurfuryl alcohol, dimethylglutarate, sulfolane, gamma-butyllactone (GBL), N, N-dimethylacetamide and mixtures thereof) A topographic photoresist removal composition is disclosed, and US Pat. No. 5,279,771 discloses a photoresist removal composition comprising hydroxylamine, alkanolamine and any polar solvent.
그러나, 상기 아민계 포토레지스트 제거용 조성물은 플라즈마 에칭 및 고온 에싱 후 잔류하는 폴리머나 이온 주입 후 경화된 포토레지스트를 완전하게 제거하지 못하는 문제가 있으며, 또한, 알루미늄과 같은 금속막의 부식 문제도 야기한다. However, the amine-based photoresist removal composition may not completely remove the polymer remaining after plasma etching and high temperature ashing or the photoresist cured after ion implantation, and also cause corrosion problems of metal films such as aluminum. .
또한, 상기와 같은 아민계 포토레지스트 제거용 조성물과는 별도로 알칼리 화합물, 카르복실산 및 물 등으로 구성된 포토레지스트 제거용 조성물이 제안되고 있다. 예를 들면, 일본 공개 특허11-125916호는, 아민, 물, α-히드록시탄산(α-Hydroxycarbonic acid), 유기용매 등으로 구성된 포토레지스트 제거용 조성물을 개시하고 있으며, 일본특개평 11-174690호는 알칸올아민, 유기산, 그리고 물로 구성된 사이드월 제거액을 개시하고 있으며, 대한민국 특허 공보 10-0503702호는 카르복실기 함유 산성 화합물, 알칸올아민류 및 특정의 제 4급 암모늄히드록시드 중에서 선택되는 1종 이상의 염기성 화합물, 함황 방식제 및 물을 함유하며, pH가 3.5~5.5인 포토레지스트 제거용 조성물을 개시하고 있다. In addition, a composition for removing a photoresist composed of an alkali compound, a carboxylic acid, water, and the like has been proposed separately from the composition for removing an amine photoresist as described above. For example, Japanese Patent Laid-Open No. 11-125916 discloses a photoresist removing composition composed of amine, water, α-Hydroxycarbonic acid, an organic solvent, and the like. No. discloses a sidewall removal liquid consisting of alkanolamine, organic acid, and water, and Korean Patent Publication No. 10-0503702 discloses one selected from carboxyl group-containing acidic compounds, alkanolamines, and certain quaternary ammonium hydroxides. The composition for photoresist removal which contains the above basic compound, a sulfur-containing anticorrosive agent, and water, and has a pH of 3.5-5.5 is disclosed.
그러나 이러한 포토레지스트 제거용 조성물은 고집적화된 반도체 소자 제조 공정 중 플라즈마 에칭 또는 고온 에싱, 그리고 이온주입 후 발생하는 폴리머 및 경화된 포토레지스트 제거성이 떨어지거나 금속막 또는 폴리 실리콘과 같은 절연막의 부식을 야기하는 문제가 있다. However, such a photoresist removal composition is inferior to plasma etching or high temperature ashing during the highly integrated semiconductor device fabrication process, and to the polymer and cured photoresist removal properties generated after ion implantation or to corrosion of an insulating film such as a metal film or polysilicon. There is a problem.
본 발명의 목적은 하드 베이킹, 플라즈마 에칭 및 고온 에싱 후 잔류하는 포토레지스트 및 포토레지스트 잔류물을 막질의 부식 없이 효과적으로 제거할 수 있는 유기계 포토레지스트 제거용 조성물을 제공하는 것이다.It is an object of the present invention to provide an organic photoresist removal composition capable of effectively removing photoresist and photoresist residues remaining after hard baking, plasma etching, and high temperature ashing without corrosion of the film.
본 발명의 목적은 생산라인 전단의 공정에서, 소오스/드레인 영역을 형성하기 위해서 불순물을 도핑하는 이온주입공정 후 경화된 포토레지스트의 박리 공정에도 탁월한 기능을 발휘하는 유기계 포토레지스트 제거용 조성물을 제공하는 것이다.SUMMARY OF THE INVENTION An object of the present invention is to provide a composition for removing an organic photoresist that has an excellent function even in a step of removing a cured photoresist after an ion implantation step of doping impurities to form a source / drain region in a process of front end of a production line. will be.
본 발명의 목적은 유기용매를 사용하여 유기물간 용해력의 향상과 알칸올아민계 화합물과의 혼합시 세정 효과를 증진시키며 아민으로 발생하는 막질의 부식을 효과적으로 제거할 수 있는 포토레지스트 제거용 조성물을 제공하는 것이다.SUMMARY OF THE INVENTION An object of the present invention is to provide a composition for removing a photoresist that can effectively remove the corrosion of the film generated by the amine and improve the dissolving power between organic substances and the cleaning effect when mixed with the alkanolamine compound using an organic solvent. It is.
본 발명은 (A) 하기 화학식 1로 표시되는 화합물 및 제4급 암모늄히드록시드로 이루어진 군으로부터 선택되는 1종 이상의 화합물; (B) 하기 화학식 2로 표시되는 화합물; (C) 하기 화학식 3으로 표시되는 화합물; (D) 당류, 당알콜류, C3~C10의 히드록시 시클로알칸 화합물, 방향족 히드록시 화합물, 아세틸렌알코올, 카르복실산 화합물, 카르복실산 화합물의 무수물 및 트리아졸 화합물로 이루어진 군으로부터 선택되는 1종 이상의 화합물; 및 (E) 알킬렌글리콜계 화합물로 이루어진 군으 로부터 선택되는 1종 이상의 유기용매 성분을 포함하는 것을 특징으로 하는 유기계 포토레지스트 제거용 조성물을 제공한다.The present invention (A) at least one compound selected from the group consisting of a compound represented by the formula (1) and a quaternary ammonium hydroxide; (B) a compound represented by the following formula (2); (C) a compound represented by the following formula (3); (D) 1 selected from the group consisting of sugars, sugar alcohols, C 3 to C 10 hydroxy cycloalkane compounds, aromatic hydroxy compounds, acetylene alcohols, carboxylic acid compounds, anhydrides of carboxylic acid compounds and triazole compounds More than one compound; And (E) at least one organic solvent component selected from the group consisting of alkylene glycol-based compounds.
<화학식 1><Formula 1>
<화학식 2><Formula 2>
<화학식 3><Formula 3>
상기 화학식 1 내지 3에서, In Chemical Formulas 1 to 3,
R1 및 R2는 각각 독립적으로 수소 또는 아미노기로 치환 또는 비치환된 C1~C10의 직쇄형 또는 분지쇄형 탄화수소이고; R 1 and R 2 are each independently C 1 to C 10 straight or branched chain hydrocarbon substituted or unsubstituted with hydrogen or an amino group;
R3는 결합 또는 C1~C10의 직쇄형 또는 분지쇄형 탄화수소이고;R 3 is a bond or a C 1 to C 10 straight or branched hydrocarbon;
R4-는 C1~C10의 직쇄형 또는 분지쇄형 탄화수소이고;R 4 -is C 1 -C 10 straight or branched chain hydrocarbon;
n 및 m은 각각 독립적으로 1 내지 5이고;n and m are each independently 1-5;
R5는 수소, C1~C5의 직쇄형 또는 분지쇄형 탄화수소 또는 1 내지 3개의 고 리(ring) 구조를 가지는 방향족 탄화수소(aromatic hydrocarbon)이고; R 5 is hydrogen, C 1 -C 5 straight or branched chain hydrocarbon or aromatic hydrocarbon having 1 to 3 ring structures;
R6는 C1~C5의 직쇄형 또는 분지쇄형 탄화수소 또는 1 내지 3개의 고리 구조를 가지는 방향족 탄화수소이고; R 6 is C 1 to C 5 straight or branched chain hydrocarbon or aromatic hydrocarbon having 1 to 3 ring structures;
R7 및 R8 는 각각 독립적으로 C1~C5의 직쇄형 또는 분지쇄형 탄화수소이고; R 7 and R 8 are each independently C 1 -C 5 straight or branched chain hydrocarbons;
R9는 수소, 또는 C1~C7의 직쇄형, 분지쇄형 또는 환형의 탄화수소이고; R 9 is hydrogen or C 1 -C 7 straight, branched or cyclic hydrocarbon;
X 및 Y는 각각 독립적으로 수소, 또는 C1~C7의 직쇄형, 분지쇄형 또는 환형의 탄화수소이거나, X와 Y는 결합하여 고리를 형성할 수 있다. X and Y are each independently hydrogen or a C 1 to C 7 linear, branched, or cyclic hydrocarbon, or X and Y may combine to form a ring.
본 발명의 유기계 포토레지스트 제거용 조성물은, 하드 베이킹, 플라즈마 에칭 및 고온 에싱 후 잔류하는 포토레지스트 및 포토레지스트 잔류물을 매우 효과적으로 제거한다. 특히 생산라인 전단의 공정에서, 소오스/드레인 영역을 형성하기 위해서 불순물을 도핑하는 이온주입공정 후 경화된 포토레지스트의 박리 공정에도 탁월한 효과를 나타낸다. 또한, 유기용매를 사용하여 유기물간 용해력의 향상과 알칸올계아민 화합물과의 혼합 시 후-세정 효과를 증진시키며 아민으로 발생하는 막질의 부식을 매우 효과적으로 제거한다.The composition for removing organic photoresists of the present invention removes photoresist and photoresist residues remaining after hard baking, plasma etching and high temperature ashing very effectively. In particular, in the process of the front end of the production line, it shows an excellent effect in the peeling process of the cured photoresist after the ion implantation process of doping the impurities to form the source / drain region. In addition, the organic solvent is used to improve the solubility between organic substances and to enhance the post-cleaning effect when mixed with the alkanol-based amine compound and to effectively remove the corrosion of the film generated by the amine.
본 발명의 유기계 포토레지스트 제거용 조성물은 (A) 하기 화학식 1로 표시되는 화합물 및 제4급 암모늄히드록시드로 이루어진 군으로부터 선택되는 1종 이 상의 화합물; (B) 하기 화학식 2로 표시되는 화합물; (C) 하기 화학식 3으로 표시되는 화합물; (D) 당류, 당알콜류, C3~C10의 히드록시 시클로알칸 화합물, 방향족 히드록시 화합물, 아세틸렌알코올, 카르복실산 화합물, 카르복실산 화합물의 무수물 및 트리아졸 화합물로 이루어진 군으로부터 선택되는 1종 이상의 화합물; 및 (E) 알킬렌글리콜계 화합물로 이루어진 군으로부터 선택되는 1종 이상의 유기용매를 포함한다.The composition for removing an organic photoresist of the present invention includes (A) at least one compound selected from the group consisting of a compound represented by the following Formula 1 and a quaternary ammonium hydroxide; (B) a compound represented by the following formula (2); (C) a compound represented by the following formula (3); (D) 1 selected from the group consisting of sugars, sugar alcohols, C 3 to C 10 hydroxy cycloalkane compounds, aromatic hydroxy compounds, acetylene alcohols, carboxylic acid compounds, anhydrides of carboxylic acid compounds and triazole compounds More than one compound; And (E) at least one organic solvent selected from the group consisting of alkylene glycol-based compounds.
<화학식 1><Formula 1>
<화학식 2><Formula 2>
<화학식 3><Formula 3>
상기 화학식 1 내지 3에서, In Chemical Formulas 1 to 3,
R1 및 R2는 각각 독립적으로 수소 또는 아미노기로 치환 또는 비치환된 C1~C10의 직쇄형 또는 분지쇄형 탄화수소이고; R 1 and R 2 are each independently C 1 to C 10 straight or branched chain hydrocarbon substituted or unsubstituted with hydrogen or an amino group;
R3는 직접결합 또는 C1~C10의 직쇄형 또는 분지쇄형 탄화수소이고;R 3 is a direct bond or a C 1 to C 10 straight or branched hydrocarbon;
R4는 C1~C10의 직쇄형 또는 분지쇄형 탄화수소이고;R 4 is C 1 -C 10 straight or branched chain hydrocarbon;
n 및 m은 각각 독립적으로 1 내지 5이고;n and m are each independently 1-5;
R5는 수소, C1~C5의 직쇄형 또는 분지쇄형 탄화수소 또는 1 내지 3개의 고리(ring) 구조를 가지는 방향족 탄화수소(aromatic hydrocarbon)이고; R 5 is hydrogen, C 1 -C 5 straight or branched chain hydrocarbon or aromatic hydrocarbon having 1 to 3 ring structures;
R6는 C1~C5의 직쇄형 또는 분지쇄형 탄화수소 또는 1 내지 3개의 고리 구조를 가지는 방향족 탄화수소이고; R 6 is C 1 to C 5 straight or branched chain hydrocarbon or aromatic hydrocarbon having 1 to 3 ring structures;
R7 및 R8는 각각 독립적으로 C1~C5의 직쇄형 또는 분지쇄형 탄화수소이고; R 7 and R 8 are each independently C 1 -C 5 straight or branched chain hydrocarbons;
R9는 수소, 또는 C1~C7의 직쇄형, 분지쇄형 또는 환형의 탄화수소이고; R 9 is hydrogen or C 1 -C 7 straight, branched or cyclic hydrocarbon;
X 및 Y는 각각 독립적으로 수소, 또는 C1~C7의 직쇄형, 분지쇄형 또는 환형의 탄화수소이거나, X와 Y는 결합하여 고리를 형성할 수 있다. X and Y are each independently hydrogen or a C 1 to C 7 linear, branched, or cyclic hydrocarbon, or X and Y may combine to form a ring.
여기서, m이 2 이상일 경우, R4는 서로 상이할 수 있다.Here, when m is 2 or more, R 4 may be different from each other.
본 발명의 유기계 포토레지스트 제거용 조성물에 포함되는 (A) 화학식 1로 표시되는 화합물 및 제4급 암모늄히드록시드로 이루어진 군으로부터 선택되는 1종 이상의 화합물은 조성물 총 중량에 대하여 1 내지 70중량%이고, 1 내지 30중량%로 포함되는 것이 바람직하다. 상술한 범위를 만족하면, 경화된 포토레지스트에 대하여 충분한 박리효과가 발휘되며, 너무 과량이 포함되어 발생할 수 있는 환경적인 문제, 오염물의 처리비용 증가 문제, 알루미늄, 구리, 티타늄과 같은 금속막을 부식시키는 문제 등을 피할 수 있다. The at least one compound selected from the group consisting of the compound represented by the formula (1) and the quaternary ammonium hydroxide included in the organic photoresist removing composition of the present invention is 1 to 70% by weight based on the total weight of the composition It is preferably included in 1 to 30% by weight. If the above-mentioned range is satisfied, sufficient peeling effect is exerted on the cured photoresist, and environmental problems that may occur due to excessive excess, increase in processing cost of contaminants, and corrosion of metal films such as aluminum, copper, and titanium Problems can be avoided.
상기 화학식 1로 표시되는 화합물은 알칸올아민인 것이 바람직하다. 상기 알칸올아민은 N-메틸에탄올아민, N-에틸에탄올아민, N-프로필에탄올아민, N-부틸에탄올아민, 모노에탄올아민, 디에탄올아민, 트리에탄올아민, N-메틸디에탄올아민, N-에틸디에탄올아민, 이소프로판올아민, 디이소프로판올아민, 트리이소프로판올아민, N-메틸이소프로판올아민, N-에틸이소프로판올아민, N-프로필이소프로판올아민, 2-아미노프로판-1-올, N-메틸-2-아미노프로판-1-올, N-에틸-2-아미노프로판-1-올, 1-아미노프로판-3-올, N-메틸-1-아미노프로판-3-올, N-에틸-1-아미노프로판-3-올, 1-아미노부탄-2-올, N-메틸-1-아미노부탄-2-올, N-에틸-1-아미노부탄-2-올, 2-아미노부탄-1-올, N-메틸-2-아미노부탄-1-올, N-에틸-2-아미노부탄-1-올, 3-아미노부탄-1-올, N-메틸-3-아미노부탄-1-올, N-에틸-3-아미노부탄-1-올, 1-아미노부탄-4-올, N-메틸-1-아미노부탄-4-올, N-에틸-1-아미노부탄-4-올, 1-아미노-2-메틸프로판-2-올, 2-아미노-2-메틸프로판-1-올, 1-아미노펜탄-4-올, 2-아미노-4-메틸펜탄-1-올, 2-아미노헥산-1-올, 3-아미노헵탄-4-올, 1-아미노옥탄-2-올, 5-아미노옥탄-4-올, 1-아미노프로판-2,3-디올, 2-아미노프로판-1,3-디올, 트리스(옥시메틸)아미노메탄, 1,2-디아미노프로판-3-올, 1,3-디아미노프로판-2-올 및 2-(2-아미노에톡시)에탄올로 이루어진 군에서 선택되는 1종 또는 2종인 것이 더 바람직하다. 이 중에서, 모노에탄올아민이 가장 바람직하다. It is preferable that the compound represented by the said Formula (1) is an alkanolamine. The alkanolamine is N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-butylethanolamine, monoethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyl Diethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, N-methylisopropanolamine, N-ethylisopropanolamine, N-propylisopropanolamine, 2-aminopropan-1-ol, N-methyl-2-aminopropane -1-ol, N-ethyl-2-aminopropan-1-ol, 1-aminopropan-3-ol, N-methyl-1-aminopropan-3-ol, N-ethyl-1-aminopropan-3 -Ol, 1-aminobutan-2-ol, N-methyl-1-aminobutan-2-ol, N-ethyl-1-aminobutan-2-ol, 2-aminobutan-1-ol, N-methyl -2-aminobutan-1-ol, N-ethyl-2-aminobutan-1-ol, 3-aminobutan-1-ol, N-methyl-3-aminobutan-1-ol, N-ethyl-3 -Aminobutan-1-ol, 1-aminobutan-4-ol, N-methyl-1-aminobutan-4-ol, N-ethyl-1-a Nobutan-4-ol, 1-amino-2-methylpropan-2-ol, 2-amino-2-methylpropan-1-ol, 1-aminopentan-4-ol, 2-amino-4-methylpentane -1-ol, 2-aminohexan-1-ol, 3-aminoheptan-4-ol, 1-aminooctan-2-ol, 5-aminooctan-4-ol, 1-aminopropan-2,3- Diol, 2-aminopropane-1,3-diol, tris (oxymethyl) aminomethane, 1,2-diaminopropan-3-ol, 1,3-diaminopropan-2-ol and 2- (2- It is more preferable that it is 1 type or 2 types chosen from the group which consists of aminoethoxy) ethanol. Of these, monoethanolamine is most preferred.
상기 제4급 암모늄히드록시드는 테트라메틸암모늄히드록시드, 테트라에틸 암모늄히드록시드, 테트라프로필암모늄히드록시드, 테트라부틸암모늄히드록시드, 트리메틸벤질암모늄히드록시드, 모노메틸트리프로필암모늄히드록시드, (2-히드록시에틸)트리프로필암모늄히드록시드 및 (1-히드록시프로필)트리메틸암모늄히드록시드로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다. 이 중에서, 테트라메틸암모늄히드록시드가 더 바람직하다.The quaternary ammonium hydroxide is tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, monomethyltripropylammonium hydroxide It is preferable that it is 1 type, or 2 or more types chosen from the group which consists of a seed, (2-hydroxyethyl) tripropyl ammonium hydroxide, and (1-hydroxypropyl) trimethyl ammonium hydroxide. Among these, tetramethylammonium hydroxide is more preferable.
본 발명의 유기계 포토레지스트 제거용 조성물에 포함되는 (B) 화학식 2로 표시되는 화합물은 조성물 총 중량에 대하여 10 내지 40 중량%로 포함되는 것이 바람직하다. 상술한 범위로 포함되면, 비아홀 주변이나 하부막에 옥사이드 잔유물이나 레지스트 폴리머등과 같은 잔유물의 우수한 제거 효과를 기대할 수 있다.The compound represented by Formula (B) 2 included in the organic photoresist removing composition of the present invention is preferably included in 10 to 40% by weight based on the total weight of the composition. When included in the above-described range, excellent removal effects of residues such as oxide residues, resist polymers, and the like can be expected in the periphery of the via holes or the lower layer.
상기 (B) 화학식 2의 화합물은 알콕시 N-히드록시알킬 알칸아미드(alkoxy N-hydroxyalkyl alkanamide)인 것이 바람직하다. 이러한 화합물의 대표적인 예로는, 3-메톡시 N-히드록시에틸 프로판아미드(화학식 2에서 R5는 수소이고, R6는 -CH2CH2- 이고, R7는 -CH2CH2- 이고, R8는 -CH3 인 경우)를 들 수 있다.The compound of Formula (B) is preferably alkoxy N-hydroxyalkyl alkanamide. Representative examples of such compounds include 3-methoxy N-hydroxyethyl propanamide (in Formula 2, R 5 is hydrogen, R 6 is —CH 2 CH 2 —, R 7 is —CH 2 CH 2 —, R 8 is -CH 3 ).
상기 (B) 화학식 2로 표시되는 화합물은 하기 반응식 1에 의해 제조될 수 있다.The compound represented by Formula (B) 2 may be prepared by the following Scheme 1.
<반응식 1><Scheme 1>
상기 반응식 1의 변수는 상기 화학식 2의 변수와 모두 동일하고, R10은 C1~C5의 탄화수소이다.The variables of Scheme 1 are all the same as the variables of Formula 2, and R 10 is a C 1 ~ C 5 hydrocarbon.
상기 반응식 1의 알칸올아민은 R5가 수소, R6가 -CH2CH2-인 모노에탄올아민(monoethanolamine)이 바람직하고, 알킬알콕시알카노에이트로는 R7가 -CH2CH2-, R8는 -CH3, R6는 -CH3인 메틸 3-메톡시 프로파노에이트(methyl 3-methoxy propanoate)가 바람직하다. The alkanolamine of Scheme 1 is preferably monoethanolamine in which R5 is hydrogen and R6 is -CH2CH2-, and alkylalkoxyalkanoate is R7 is -CH2CH2-, R8 is -CH3, and R6 is -CH3. Preference is given to methyl 3-methoxy propanoate.
이 때, 반응이 일어나기에 충분한 에너지를 공급하기 위해서 반응 온도는 상온 내지 120℃로 유지하고, 80℃ 내지 90℃인 것이 바람직하다.At this time, in order to supply sufficient energy for the reaction to occur, the reaction temperature is preferably maintained at room temperature to 120 ° C, and preferably 80 ° C to 90 ° C.
상기 반응식 1에서 알 수 있는 바와 같이, 아민과 에스테르를 반응시키면 아미드가 생성됨과 동시에 알코올이 생성된다. 상기 알코올은 탄소수 1 내지 5개의 알코올로 끓는 점이 낮은 물질(예: 메탄올의 끓는 점은 약 60℃임)인 반면, 아미드는 끓는 점이 높은 물질(예: 메톡시 N-히드록시에틸 프로판아미드의 경우 끓는 점이 약 200℃임)이다. 따라서, 분별 증류법으로 알코올(V)을 제거하여 아미드 화합물을 수득한다. 분별 증류시 반응조내에 질소 버블링(bubbling) 처리를 하여 분별 증류를 촉진하거나 반응조 내의 압력을 감압하여 알코올의 기화를 촉진하는 것이 바람직하다. 물론 두 가지 방법을 동시에 사용할 수도 있다.As can be seen in Scheme 1, the reaction between the amine and the ester produces an amide and at the same time an alcohol. The alcohol is a low-boiling substance (e.g. methanol has a boiling point of about 60 ° C.) with 1 to 5 carbon atoms, while the amide is a high boiling substance (e.g. methoxy N-hydroxyethyl propanamide). Boiling point is about 200 ° C.). Thus, alcohol (V) is removed by fractional distillation to give an amide compound. In the case of fractional distillation, it is preferable to facilitate the fractional distillation by nitrogen bubbling treatment in the reactor or to reduce the pressure in the reactor to promote vaporization of alcohol. Of course, you can use both methods at the same time.
본 발명의 유기계 포토레지스트 제거용 조성물에 포함되는 (C) 화학식 3으로 표시되는 화합물은 조성물 총 중량에 대하여 0.1 내지 20 중량%로 포함되는 것 이 바람직하다. 상술한 범위로 포함되면, 고온 에싱 후 잔류하는 포토레지스트 및 포토레지스트 잔류물을 제거하는데 탁월한 효과를 기대할 수 있다.The compound represented by the formula (C) 3 included in the organic photoresist removing composition of the present invention is preferably included in 0.1 to 20% by weight based on the total weight of the composition. When included in the above-described range, excellent effects can be expected in removing photoresist and photoresist residues remaining after high temperature ashing.
상기 (C) 화학식 3으로 표시되는 화합물은 히드록실아민, N-메틸히드록실아민, N-에틸히드록실아민 및 N,N-디에틸히드록실아민으로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다. 이 중에서, 히드록실아민이 더 바람직하다.The compound represented by the formula (C) is one or two or more selected from the group consisting of hydroxylamine, N-methylhydroxylamine, N-ethylhydroxylamine and N, N-diethylhydroxylamine It is preferable. Among these, hydroxylamine is more preferable.
본 발명의 유기계 포토레지스트 제거용 조성물에 포함되는 (D) 당류, 당알콜류, 방향성 히드록시 화합물, 알킨알코올, 카르복실산 화합물, 카르복실산 화합물의 무수물 및 트리아졸 화합물로 이루어진 군으로부터 선택되는 1종 이상의 화합물은 조성물 총 중량에 있어서, 1 내지 40중량%로 포함되는 것이 바람직하다. 상술한 범위로 포함되면, 알루미늄, 구리, 티타늄과 같은 금속막에 대한 부식 방지 효과가 충분히 발휘되며, 너무 과량 포함되어 아민의 활동도를 저하시키는 문제를 피할 수 있다.1 selected from the group consisting of (D) sugars, sugar alcohols, aromatic hydroxy compounds, alkyn alcohols, carboxylic acid compounds, anhydrides of carboxylic acid compounds and triazole compounds included in the organic photoresist removing composition of the present invention. The at least one compound is preferably included in an amount of 1 to 40% by weight based on the total weight of the composition. When included in the above-described range, the anti-corrosion effect on the metal film such as aluminum, copper, and titanium is sufficiently exhibited, and it is possible to avoid the problem of excessively included so as to lower the activity of the amine.
상기 당류는 글리세린 알데히드, 아스코르빈산, 이소(iso-)아스코르빈산, 트레오즈, 아라비노스, 크실로스, 리보스, 리불로스(ribulose), 크실루로스(xylulose), 글루코스, 만노스, 갈락토스, 타가토스, 알로스, 알트로스, 굴로스(gulose), 이도스(idose), 탈로스(talose), 소르보스(sorbose), 사이코스(psicose), 프룩토스 같은 탄소수 3 내지 6의 단당류와; 트리할로스(trihalose) 같은 2당류로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다.The sugars are glycerin aldehyde, ascorbic acid, iso (iso-) ascorbic acid, threose, arabinose, xylose, ribose, ribulose, xylulose, glucose, mannose, galactose, taga Monosaccharides having 3 to 6 carbon atoms, such as toss, allose, altrose, gulose, idose, talos, sorbose, psicose, and fructose; It is preferably one or two or more selected from the group consisting of disaccharides such as trihalose.
상기 당알콜류는 트레이톨(threitol), 에리쓰리톨(erythritol), 아도니톨, 아라비톨, 크실리톨, 탈리톨, 소르비톨, 만니톨, 이디톨(iditol), 둘시톨(dulcitol) 및 이노시톨(inositol)로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다. The sugar alcohols include threitol, erythritol, adonitol, arabitol, xylitol, thalitol, sorbitol, mannitol, iditol, dulcitol and inositol It is preferable that it is 1 type, or 2 or more types chosen from the group which consists of).
상기 C3~C10의 히드록시 시클로알칸 화합물은 사이클로헥산-1,4-디메탄올인 것이 바람직하다.The hydroxy cycloalkane compound of C 3 to C 10 is preferably cyclohexane-1,4-dimethanol.
상기 방향족 히드록시 화합물은 페놀, 크레졸, 크실레놀, 피로카테콜(pyrocatechol), 레조르시놀, 히드로퀴논, 피로갈롤(pyrogallol), 1,2,4-벤젠트리올, 살리실알코올, p-히드록시벤질 알코올, p-히드록시페네틸 알코올, p-아미노페놀, m-아미노페놀, 디아미노페놀, 아미노레조르시놀, p-히드록시벤조산, o-히드록시벤조산, 2,4-디히드록시벤조산, 2,5-디히드록시벤조산, 3,4-디히드록시벤조산, 3,5-디히드록시벤조산 및 갈릭산로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다.The aromatic hydroxy compound is phenol, cresol, xylenol, pyrocatechol, resorcinol, hydroquinone, pyrogallol, 1,2,4-benzenetriol, salicyl alcohol, p-hydride Hydroxybenzyl alcohol, p-hydroxyphenethyl alcohol, p-aminophenol, m-aminophenol, diaminophenol, aminoresorcinol, p-hydroxybenzoic acid, o-hydroxybenzoic acid, 2,4-dihydroxy It is preferable that it is 1 type, or 2 or more types chosen from the group which consists of benzoic acid, 2, 5- dihydroxy benzoic acid, 3, 4- dihydroxy benzoic acid, 3, 5- dihydroxy benzoic acid, and gallic acid.
상기 알킨알코올은 에틴알코올, 2-부틴-1,4-디올, 3,5-디메틸-1-헥신-3-올, 2-메틸-3-부틴-2-올, 3-메틸-1-펜틴-3-올, 3,6-디메틸-4-옥틴-3,6-디올, 2,4,7,9-테트라메틸-5-데신(decin)-4,7-디올 및 2,5-디메틸-3-헥신-2,5-디올로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다.The alkyn alcohols include ethynal alcohol, 2-butyne-1,4-diol, 3,5-dimethyl-1-hexyn-3-ol, 2-methyl-3-butyn-2-ol, 3-methyl-1-pentin -3-ol, 3,6-dimethyl-4-octin-3,6-diol, 2,4,7,9-tetramethyl-5-decin-4,7-diol and 2,5-dimethyl It is preferable that it is 1 type (s) or 2 or more types chosen from the group which consists of -3-hexine-2,5-diol.
상기 카르복실산 화합물과 이의 무수물은 포름산, 아세트산, 프로피온산, 부티르산, 이소부티르산, 옥살산, 말론산, 숙신산, 글루타르산, 말레산, 푸마르산, 벤조산, 프탈산, 1,2,3-벤젠트리카르복실산, 글리콜산, 디글리콜산, 락트산, 말릭산, 시트르산, 아세트산무수물, 프탈산무수물, 말레산무수물, 숙신산 무수물 및 살리실산로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다.The carboxylic acid compound and its anhydride are formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, maleic acid, fumaric acid, benzoic acid, phthalic acid, 1,2,3-benzenetricarboxyl The acid, glycolic acid, diglycolic acid, lactic acid, maleic acid, citric acid, acetic anhydride, phthalic anhydride, maleic anhydride, and one or two or more selected from the group consisting of succinic anhydride and salicylic acid are preferable.
상기 트리아졸 화합물은 벤조트리아졸, o-톨릴트리아졸, m-톨릴트리아졸, p-톨릴트리아졸, 카르복시벤조트리아졸, 1-히드록시벤조트리아졸, 니트로벤조트리아졸 및 디히드록시프로필벤조트리아졸로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다. The triazole compound is benzotriazole, o-tolyltriazole, m-tolyltriazole, p-tolyltriazole, carboxybenzotriazole, 1-hydroxybenzotriazole, nitrobenzotriazole and dihydroxypropylbenzo It is preferable that it is 1 type, or 2 or more types chosen from the group which consists of a triazole.
상기 (D) 성분은 소르비톨, 만니톨, 이디톨(iditol), 둘시톨(dulcitol) 및 이노시톨(inositol)로 이루어진 당알콜류로부터 선택되는 1종 또는 2종 이상인 것이 더 바람직하다.It is more preferable that the said (D) component is 1 type, or 2 or more types chosen from sugar alcohols which consist of sorbitol, mannitol, iditol, dulcitol, and inositol.
본 발명의 유기계 포토레지스트 제거용 조성물에 포함되는 (E) 알킬렌글리콜계 화합물로 이루어진 군으로부터 선택되는 1종 이상의 유기용매는 조성물 총 중량에 대하여 5 내지 30 중량%로 포함되는 것이 바람직하다. 상술한 범위를 만족하면, 경화되거나 폴리머로 변질된 포토레지스트의 박리 역할을 하는 화합물의 활동도를 떨어뜨리는 문제를 피할 수 있으며, 박리 효과를 나타내는 다른 화합물의 함량을 상대적으로 감소시켜 박리 효과를 저하시키거나 금속막 부식이 야기되는 문제를 피할 수 있다. At least one organic solvent selected from the group consisting of (E) alkylene glycol-based compounds included in the organic photoresist removing composition of the present invention is preferably included in an amount of 5 to 30% by weight based on the total weight of the composition. When the above-mentioned range is satisfied, the problem of degrading the activity of the compound that serves as the peeling of the cured or polymer-modified photoresist can be avoided, and the content of other compounds exhibiting the peeling effect is relatively decreased, thereby lowering the peeling effect. Can be avoided or problems caused by metal film corrosion.
상기 알킬렌글리콜계 화합물은 에틸렌글리콜, 디에틸렌글리콜, 트리에틸렌글리콜, 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸글리콜, 프로필렌글리 콜모노메틸에테르, 부틸렌글리콜, 디부틸렌글리콜, 트리부틸렌글리콜, 디프로필렌글리콜모노메틸에테르 및 트리프로필렌글리콜모노메틸에테르로 이루어진 군에서 선택되는 1종 또는 2종 이상인 것이 바람직하다. 이 중에서 에틸렌글리콜인 것이 더 바람직하다.The alkylene glycol-based compound is ethylene glycol, diethylene glycol, triethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl glycol, propylene glycol monomethyl ether, butylene glycol, dibutylene glycol, tributylene glycol It is preferable that it is 1 type, or 2 or more types chosen from the group which consists of a dipropylene glycol monomethyl ether, and a tripropylene glycol monomethyl ether. Among these, ethylene glycol is more preferable.
본 발명의 유기계 포토레지스트 제거용 조성물은 유기계이므로 탈이온수를 사용하지 않는다. Since the organic photoresist removing composition of the present invention is organic, deionized water is not used.
본 발명의 유기계 포토레지스트 제거용 조성물은 상기에서 언급한 화합물을 소정량으로 유리하게 혼합하여 제조될 수 있으며 혼합 방법은 특별히 제한되지 않으며 여러가지 공지방법을 적용할 수 있다.The composition for removing an organic photoresist of the present invention may be prepared by advantageously mixing the above-mentioned compounds in a predetermined amount, and the mixing method is not particularly limited and various known methods may be applied.
본 발명의 유기계 포토레지스트 제거용 조성물을 이용한 박리방법은 당 업계에 통상적으로 알려진 방법에 의하여 수행될 수 있으며, 포토레지스트 제거용 조성물과 경화되거나 폴리머로 변질된 포토레지스트가 있는 기판이 접촉할 수 있는 방법이면 양호한 결과를 얻을 수 있다. 본 발명에 따른 박리방법으로는 침적, 분무, 또는 침적 및 분무를 이용한 방법 등이 적용된다. 침적, 분무, 또는 침적 및 분무에 의하여 박리하는 경우, 박리 조건으로서 온도는 대개 10 내지 100℃, 바람직하게는 20 내지 80℃이고, 침적, 분무, 또는 침적 및 분무 시간은 대개 30초 내지 180분, 바람직하게는 1분 내지 20분이지만, 본 발명에 있어서 엄밀하게 적용되지는 않으며, 당업자에 의해 적절하게 선택될 수 있다. The peeling method using the composition for removing the organic photoresist of the present invention may be performed by a method commonly known in the art, and the substrate having the photoresist cured or modified with a polymer may be contacted with the photoresist removing composition. If it is a method, a favorable result can be obtained. As the peeling method according to the present invention, deposition, spraying, or a method using deposition and spraying is applied. When delamination by spraying, spraying, or immersion and spraying, the temperature is usually 10 to 100 ° C., preferably 20 to 80 ° C., and the immersion, spray, or immersion and spraying time is usually 30 seconds to 180 minutes. Preferably, it is 1 to 20 minutes, but is not strictly applied in the present invention, and may be appropriately selected by those skilled in the art.
이하에서, 실시예를 통하여 본 발명을 보다 상세히 설명한다. 그러나, 하기의 실시예는 본 발명을 더욱 구체적으로 설명하기 위한 것으로서, 본 발명의 범위가 하기의 실시예에 의하여 한정되는 것은 아니다. 하기의 실시예는 본 발명의 범위 내에서 당업자에 의해 적절히 수정, 변경될 수 있다. Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are intended to illustrate the present invention more specifically, but the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.
실시예1 내지 실시예4, 비교예1 내지 비교예6: 포토레지스트 제거용 조성물의 제조Examples 1-4, Comparative Examples 1-6: Preparation of Photoresist Removal Composition
하기 표 1 및 표 2와 같은 성분들을 정해진 함량으로 혼합하여 실시예1 내지 4 및 비교예1 내지 6의 포토레지스트 제거용 조성물을 제조하였다. 표 1 및 표 2에서 함량의 단위는 모두 중량%이다.To prepare a composition for removing the photoresist of Examples 1 to 4 and Comparative Examples 1 to 6 by mixing the components shown in Table 1 and Table 2 in a predetermined amount. In Table 1 and Table 2, the units of the content are all in weight percent.
MEA: 모노에탄올아민 TMAH: 테트라메틸암모늄히드록시드MEA: monoethanolamine TMAH: tetramethylammonium hydroxide
NHAA(N-히이드록시알킬 알칸아미드): 3-메톡시 N-히드록시에틸 프로판아미드NHAA (N-hydroxyalkyl alkanamide): 3-methoxy N-hydroxyethyl propanamide
HA: 히드록시아민 DGA: 다이글리콜아민HA: hydroxyamine DGA: diglycolamine
APM: 아미노프로필몰포린 MDEA: 메틸디에탄올아민APM: aminopropylmorpholine MDEA: methyldiethanolamine
MMP: 메틸메톡시프로파노에이트 EDA: 에틸렌다이아민MMP: Methylmethoxypropanoate EDA: Ethylenediamine
AEEA: 아미노에틸에탄올아민 MMEA: 모노메틸에탄올아민AEEA: aminoethylethanolamine MMEA: monomethylethanolamine
시험예 1: 박리 능력 및 부식성 테스트Test Example 1: Peeling ability and corrosion test
플라즈마 에칭 또는 고온 에싱 후 경화된 포토레지스트막과 잔류 잔사물이 금속막 또는 절연막에 응착된 시편을 온도 65℃의 실시예 및 비교예의 포토레지스트 제거용 조성물에 20분간 침적시켰다. 그 후, 박리액으로부터 시편을 꺼내고 초순수로 1분간 린스한 후, 질소 가스를 이용하여 건조시켰다. 그리고 주사전자현미경을 이용하여 경화된 포토레지스트막과 잔류 잔사물의 제거성과 약액에 노출된 금속막 및 절연막의 부식성을 평가하였다. 제거성 및 부식성 평가는 다음과 같은 기준에 의하여 실시하였으며, 그 결과는 하기의 표 3에 나타내었다.After the plasma etching or high temperature ashing, the cured photoresist film and the remaining residue adhered to the metal film or the insulating film were immersed in the photoresist removing composition of Examples and Comparative Examples at a temperature of 65 ° C. for 20 minutes. Thereafter, the specimen was removed from the stripping solution, rinsed with ultrapure water for 1 minute, and then dried using nitrogen gas. In addition, the scanning electron microscope was used to evaluate the removal of the cured photoresist film and residual residue and the corrosion of the metal film and the insulating film exposed to the chemical liquid. Removal and corrosion evaluation was performed according to the following criteria, the results are shown in Table 3 below.
<박리 능력 평가 기준>Peeling ability evaluation criteria
O: 메탈, 패드, 비아홀 주변이나 표면에 남아 있는 폴리머가 완전하게 제거된 경우O: Any polymer remaining around or on the metal, pads, or via-holes is completely removed.
△: 메탈, 패드, 비아홀 주변이나 표면에 남아 있는 폴리머가 70% 이상 제거된 경우△: 70% or more of polymer remaining around or on the surface of metal, pad, via hole
X: 메탈, 패드, 비아홀 주변이나 표면에 남아 있는 폴리머가 거의 제거되지 않은 경우X: Almost no polymer remaining around or on metal, pads, or via-holes
<부식성 평가 기준>Corrosion Evaluation Criteria
O: 메탈, 패드의 상하부, 비아홀 주변이나 하부막에 부식이 없는 경우O: When there is no corrosion in the metal, upper and lower parts of the pad, around the via hole or the lower film
△: 메탈, 패드의 상하부, 비아홀 주변이나 하부막에 부식이 있는 경우(Triangle | delta): When metal, upper and lower parts of a pad, a via hole, or a lower film | membrane has corrosion.
X: 메탈, 패드의 상하부, 비아홀 주변이나 하부막에 부식이 심한 경우X: High corrosion on metal, upper and lower parts of pad, via hole or lower
표 3을 참조하면, 본 발명의 유기계 포토레지스트 제거용 조성물은 박리성 및 부식성에 있어서 수계 포토레지스트 제거용 조성물 대비하여 우수한 기능을 나타냈다. 그러나, 비교예의 조성물들은 박리성과 부식성 중 하나 이상에 있어서 부족한 기능을 나타냈다.Referring to Table 3, the composition for removing the organic photoresist of the present invention showed excellent function compared to the composition for removing the aqueous photoresist in peelability and corrosion. However, the compositions of the comparative examples showed poor function in at least one of peelability and corrosiveness.
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